I listen to the Dead out of my iPod, and what would be the best and comfortable pair of headphones for listening to the Dead on a daily basis with overall outstanding sound quality? I have a pair of Sennheiser HD 202. Would someone recommend better quality then the HD 202? I have to admit the HD 202 pair are very uncomfortable on my ears for both short and long period of using them.

I've been using Grado SR-80s for a long time and love them. Many don't like the can or open air style. If comfort is more important, I like the Bose IE2s, though they change the sound dynamics quite a bit. Both are in the $100 range. FWIW - The SR-80s were ranked highest in Consumer Reports, beating out those in the $400 range.

Good headphones will help but keep in mind that the mp3 format is going to limit your listening clarity and fidelity. Mp3 really limits the sound quality, but for portable music they don't give us a lot of format options these days. CD or some sort of lossless audio file on your computer would be a better option if you don't need the portability.